CN114149325B - Method for preparing beta-methoxy fatty acid ester by using olefin and methyl formate under promotion of visible light - Google Patents
Method for preparing beta-methoxy fatty acid ester by using olefin and methyl formate under promotion of visible light Download PDFInfo
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- CN114149325B CN114149325B CN202010934913.6A CN202010934913A CN114149325B CN 114149325 B CN114149325 B CN 114149325B CN 202010934913 A CN202010934913 A CN 202010934913A CN 114149325 B CN114149325 B CN 114149325B
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- olefin
- methyl formate
- visible light
- fatty acid
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- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 19
- 238000000034 method Methods 0.000 title claims abstract description 17
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 15
- 239000000194 fatty acid Substances 0.000 title claims abstract description 15
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 15
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 30
- 239000011941 photocatalyst Substances 0.000 claims abstract description 12
- PRWATGACIORDEL-UHFFFAOYSA-N 2,4,5,6-tetra(carbazol-9-yl)benzene-1,3-dicarbonitrile Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=C(C#N)C(N2C3=CC=CC=C3C3=CC=CC=C32)=C(N2C3=CC=CC=C3C3=CC=CC=C32)C(N2C3=CC=CC=C3C3=CC=CC=C32)=C1C#N PRWATGACIORDEL-UHFFFAOYSA-N 0.000 claims abstract description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052786 argon Inorganic materials 0.000 claims abstract description 3
- 150000003222 pyridines Chemical class 0.000 claims abstract description 3
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 7
- 239000012300 argon atmosphere Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- 238000005303 weighing Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 7
- 229910052751 metal Inorganic materials 0.000 abstract description 3
- 239000002184 metal Substances 0.000 abstract description 3
- 125000001424 substituent group Chemical group 0.000 abstract description 2
- 239000007800 oxidant agent Substances 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- -1 Ester compounds Chemical class 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 4
- 238000006555 catalytic reaction Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000007146 photocatalysis Methods 0.000 description 3
- 230000001699 photocatalysis Effects 0.000 description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 3
- LTVRSJBNXLZFGT-UHFFFAOYSA-N 2-silylethenone Chemical compound [SiH3]C=C=O LTVRSJBNXLZFGT-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 102000009410 Chemokine receptor Human genes 0.000 description 1
- 108050000299 Chemokine receptor Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- YVBSAPDHRXHFHV-UHFFFAOYSA-N [chloro(methoxy)methyl]benzene Chemical compound COC(Cl)C1=CC=CC=C1 YVBSAPDHRXHFHV-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000005349 anion exchange Methods 0.000 description 1
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000014101 wine Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Catalysts (AREA)
Abstract
The invention relates to a method for preparing beta-methoxy fatty acid ester by using olefin and methyl formate, which is promoted by visible light, and concretely comprises the steps of taking olefin as a raw material under irradiation of visible light, taking pyridine salts with different substituents as an oxidant, taking methyl formate as a solvent, taking 4CzIPN as a photocatalyst under the atmosphere of argon, and reacting for 1h at room temperature under irradiation of blue LEDs. Compared with other traditional methods, the method has the characteristics of no metal participation, greenness, mild reaction conditions, good selectivity and the like, and therefore, the method has good industrial application prospect.
Description
Technical Field
The invention relates to a method for preparing beta-methoxy fatty acid ester by using alkene and methyl formate under the promotion of visible light.
Background
Ester compounds are used in a large number in the industries of wines, foods, cosmetics, detergents, surfactants and the like. The beta-methoxy fatty acid ester can be used for preparing derivatives (U.S. patent 6,649,606[ P ] 2003-11-18 ]) such as anti-inflammatory drugs, which are extremely valuable modulators of chemokine receptor activity, and has high medicinal value in medicine. In addition, beta-methoxy fatty acids can be easily beta-eliminated, producing alpha, beta-unsaturated lipids, and are of great interest in the synthesis of complex bioactive compounds. (Angew. Chem. Int. Ed.2019,58, 10305-10309)
The beta-methoxy fatty acid ester is taken as a compound with extremely high application value, and the current preparation strategies mainly comprise the following steps:
in 2014, berkessel and colleagues reported a method for preparing beta-methoxy fatty acid esters by catalyzing alpha-methoxybenzyl chloride with silyl ketene acetals with pyridinium cations. The chloride is ionized under the pyridinium cation, followed by anion exchange. The resulting oxocarbonium-tetraphenylborate ion pair is subjected to nucleophilic attack by silyl ketene acetals to yield the desired product. The implementation of the system requires extreme conditions of ultra-low temperature and relatively complex substrates, and therefore, the method has disadvantages in practical applications (angel. Chem. Int. Ed.2014,53, 11660-11664). In 2016, the Ukaji group reported that beta-methoxy fatty acid esterification of vinyl phenol was achieved by palladium catalysis using CO as the carbonyl source and alcohol as the affinity reagent. The reaction requires not only a relatively high temperature and catalysis by the transition metal, but also the substrate of the reaction is limited to vinyl phenol (chem. Lett.2016,45, 1431-1433). In 2019, jieping Zhu task group reported that the preparation of β -methoxy fatty acid esters and five membered heterocycles from olefins was achieved using methyl formate as a source of methoxy and methoxycarbonyl groups under copper catalysis. However, this reaction requires a relatively high temperature and a metal complex as a catalyst, so that it has a certain disadvantage in green chemistry (angel. Chem. Int. Ed.2019,58, 10305-10309).
These processes either require transition metal catalysis or require more severe conditions to perform. Therefore, a photocatalysis path with mild conditions is adopted, and the formic ether which is cheap and easy to obtain is used as a precursor to generate an alkoxycarbonyl free radical, so that the methoxycarbonyl of olefin is realized, and the method has very good application prospect in the fields of fine chemical engineering, pharmaceutical chemistry, material science and the like.
Disclosure of Invention
It is an object of the present invention to provide a visible light-promoted process for the preparation of beta-methoxy fatty acid esters using olefins and methyl formate. The invention does not need to use metal additives, and has good industrial application prospect.
The method for preparing beta-methoxy fatty acid ester by using olefin and methyl formate, which is promoted by visible light, comprises the following steps:
1) The photocatalyst 4CzIPN and pyridinium were weighed and added to the reaction tube and argon was replaced three times by vacuum line.
2) Under argon atmosphere, α -methylstyrene, methyl formate was carefully added.
3) The reaction tube was then placed under irradiation of a 12W blue LEDs lamp and allowed to react for 1h at room temperature.
The olefin used is an aromatic or heteroaromatic substituted olefin.
The pyridine salt compounds containing different substituents are:
the photocatalyst used was 4CzIPN.
The solvent used was methyl formate.
The light sources used are all visible light.
Further, the molar ratio of olefin, pyridine salt and photocatalyst is 1:2.5:0.03.
Further, the concentration of the substrate olefin of the reaction system was 0.017M.
Compared with the prior art, the invention has the remarkable advantages that:
1. according to the invention, under the condition of no metal participation, through a green path of photocatalysis by light and organic micromolecules, an oxygen free radical generated by pyridinium under the photocatalysis is utilized to abstract inert hydrogen of methyl formate, an alkoxycarbonyl free radical is generated, the alkoxycarbonyl free radical is subjected to addition reaction with olefin and is subjected to in-situ generated methanol reaction of methyl formate under the illumination condition, the beta-methoxy fatty acid ester compound can be simply and efficiently prepared, and better chemical selectivity and functional group tolerance are shown; 2. the invention can effectively modify complex drug molecules and compounds, and has great significance for medicine research and development.
Detailed Description
The following specific embodiments of the present invention are provided, and it should be noted that the present invention is not limited to the following specific embodiments, and all equivalent changes made on the basis of the technical solutions of the present application fall within the protection scope of the present invention.
Example 1
The photocatalyst 4CzIPN (2.4 mg, 0.003mmol) and 4-cyano-1-methoxypyridin-1-yl tetrafluoroborate (55 mg,0.25 mmol) were weighed into a reaction tube, air was extracted three times by vacuum line, alpha-methylstyrene (0.1 mmol,11.8 mg) and methyl formate 6ml were carefully added under argon atmosphere, and then the reaction tube was placed under irradiation of a 12W blue LED lamp, chamberThe reaction was carried out at a temperature for 1h. At the end of the reaction, the mixture was quenched with water and extracted with ethyl acetate (3X 5 ml). The organic phase was dried over anhydrous sodium sulfate and then distilled off in vacuo to remove the solvent, loaded in wet mode, and subjected to column chromatography (300-400 mesh silica gel chromatography) (eluent: petroleum ether-ethyl acetate, volume ratio: 25-15:1) to give 11.0mg of the product in 53% yield. 1 H NMR(500MHz,CDCl 3 )δ7.42-7.33(m,4H),δ7.30-7.25(m,1H),3.59(s,3H),3.10(s,3H),2.84(d,J＝13.7Hz,1H),2.74(d,J＝13.7Hz,1H),1.74(s,3H).
Example 2
The photocatalyst 4CzIPN (2.4 mg, 0.003mmol) and 4-cyano-1-ethoxypyridin-1-yl tetrafluoroborate (59 mg,0.25 mmol) were weighed first, added to the reaction tube, air was extracted three times by vacuum line, α -methylstyrene (0.1 mmol,11.8 mg) was carefully added under argon atmosphere, methyl formate 6ml, and then the reaction tube was placed under irradiation of 12W blue LEDs for reaction at room temperature for 12h. At the end of the reaction, the mixture was quenched with water and extracted with ethyl acetate (3X 5 ml). The organic phase was dried over anhydrous sodium sulfate and then distilled off in vacuo to remove the solvent, loaded in wet mode, and subjected to column chromatography (300-400 mesh silica gel chromatography) (eluent: petroleum ether-ethyl acetate, volume ratio: 25-15:1) to give 15.0mg of the product in 72% yield.
Example 3
The photocatalyst 4CzIPN (2.4 mg, 0.003mmol) and 4-cyano-1-isopropoxypyridin-1-yl triflate (78 mg,0.25 mmol) were weighed into a reaction tube, air was extracted three times by vacuum line, α -methylstyrene (0.1 mmol,11.8 mg) was carefully added under argon atmosphere, methyl formate 6ml, and then the reaction tube was placed under 12W blue LEDs lamp irradiation, and reacted for 1h at room temperature. At the end of the reaction, the mixture was quenched with water and extracted with ethyl acetate (3X 5 ml). The organic phase was dried over anhydrous sodium sulfate and then distilled off in vacuo to remove the solvent, loaded in wet mode, and subjected to column chromatography (300-400 mesh silica gel chromatography) (eluent: petroleum ether-ethyl acetate, volume ratio: 25-15:1) to give 16.7mg of the product in 80% yield.
Example 4
The photocatalyst 4CzIPN (2.4 mg, 0.003mmol) and 4-methyl-1-isopropoxypyridin-1-yl triflate (75 mg,0.25 mmol) were weighed into a reaction tube, air was extracted three times by vacuum line, α -methylstyrene (0.1 mmol,11.8 mg) was carefully added under argon atmosphere, methyl formate 6ml, and then the reaction tube was placed under 12W blue LEDs lamp irradiation, and reacted for 1h at room temperature. At the end of the reaction, the mixture was quenched with water and extracted with ethyl acetate (3X 5 ml). The organic phase was dried over anhydrous sodium sulfate and then distilled off in vacuo to remove the solvent, loaded in wet mode, and subjected to column chromatography (300-400 mesh silica gel chromatography) (eluent: petroleum ether-ethyl acetate, volume ratio: 25-15:1) to give 14.6mg of the product in 70% yield.
Example 5
The photocatalyst 4CzIPN (2.4 mg, 0.003mmol) and 1-isopropoxypyridin-1-yl triflate (72 mg,0.25 mmol) were weighed into a reaction tube, air was extracted three times by vacuum line, α -methylstyrene (0.1 mmol,11.8 mg) was carefully added under argon atmosphere, methyl formate 6ml, and then the reaction tube was placed under irradiation of 12W blue LEDs for reaction at room temperature for 1h. At the end of the reaction, the mixture was quenched with water and extracted with ethyl acetate (3X 5 ml). The organic phase was dried over anhydrous sodium sulfate and then distilled off in vacuo to remove the solvent, loaded in wet mode, and subjected to column chromatography (300-400 mesh silica gel chromatography) (eluent: petroleum ether-ethyl acetate, volume ratio: 25-15:1) to give 13.5mg of the product in 65% yield.
Claims (6)
1. A method for preparing beta-methoxy fatty acid ester by using alkene and methyl formate under the promotion of visible light, which is characterized by comprising the following steps:
1) Weighing a photocatalyst 4CzIPN and pyridinium, adding the photocatalyst and pyridinium into a reaction tube, and replacing argon for three times through a vacuum line;
2) Under argon atmosphere, adding alpha-methyl styrene and methyl formate;
3) Then, the reaction tube is placed under the irradiation of visible light to react for 1h at room temperature;
the light source used is a 12W blue LED lamp;
the pyridinium salt used is one of the following five types:
2. the preparation method according to claim 1, characterized in that the reaction is as follows:
3. the preparation method according to claim 1, wherein the molar ratio of the olefin, the pyridine salt and the photocatalyst is 1:2.5:0.03.
4. The process of claim 1 wherein the concentration of substrate olefin is 0.017M.
5. The process of claim 1 wherein the olefin is an aromatic or heteroaromatic substituted olefin.
6. The method according to claim 1, wherein the product of the reaction system is a beta-methoxy fatty acid ester having an aromatic or heteroaromatic substituent at the beta position.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109293541A (en) * | 2018-11-09 | 2019-02-01 | 闽南师范大学 | A kind of visible light catalytic prepares alpha-aromatic-γ-methylsulfinyl ketone compounds method |
| CN110386885A (en) * | 2019-07-30 | 2019-10-29 | 曲阜师范大学 | A kind of visible light promotion β-carbonyl sulphones preparation method |
| CN111559992A (en) * | 2020-05-29 | 2020-08-21 | 华中科技大学 | Preparation method of 2-aryl-gamma-aminobutyric acid derivative |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109293541A (en) * | 2018-11-09 | 2019-02-01 | 闽南师范大学 | A kind of visible light catalytic prepares alpha-aromatic-γ-methylsulfinyl ketone compounds method |
| CN110386885A (en) * | 2019-07-30 | 2019-10-29 | 曲阜师范大学 | A kind of visible light promotion β-carbonyl sulphones preparation method |
| CN111559992A (en) * | 2020-05-29 | 2020-08-21 | 华中科技大学 | Preparation method of 2-aryl-gamma-aminobutyric acid derivative |
Non-Patent Citations (1)
| Title |
|---|
| Copper-Catalyzed 1,2-Methoxy Methoxycarbonylation of Alkenes with Methyl Formate;Balazs Budai等;Angew. Chem. Int. Ed.;第58卷;10305-10309 * |
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